The reason you wait until the deadline to extend is because you prefer heavily to trade the player and you want to create a more dynamic situation where things are fluid and other teams perceive that you might keep the player. If you negotiate in January, and the player ends up on the market, there's no added leverage. Everybody knows re-signing is off the table.
It isn't exactly unprecedented for a team to keep a rental because offers are really bad. On a recent episode of Tim and Sid, Brian Burke discussed how teams have to set their prices internally before the deadline. He claimed that the Flames decided to keep Cammalleri because internally they set a price of a 1st and they didn't get it. They had relented and decided they'd accept a 2nd, but the best offer was a 3rd, so they kept him. I also recall Vancouver doing the same thing when nobody paid up for Bieksa in 2015. In both situations, neither the Flames or Canucks were playoff teams.
That doesn't justify it. I think it is a stupid move. Especially since we're basically done selling off our top assets from the past build. So it's difficult to even justify from a point of view that by keeping Pageau, Dorion is building social capital with other GMs who will then understand if they want his good pieces, they have to come closer to meeting his price. Unless we're moving our young guys, our good pieces will almost all have been sold off.
Dorion is the same person who has raved about the top 60 of this draft, so if there is a top 60 pick on the table for Pageau, and that's the best offer, I don't understand why he wouldn't take it. If the idea is to get a contract done later on, why not revisit things in the summer when Pageau becomes a UFA? If we can't come to an understanding now, how likely are we to come to an understanding before the UFA talking period opens up at the end of June? If Pageau goes somewhere else, maybe it gives him some further perspective on his fit in Ottawa, and maybe it helps our case with getting him to sign our version of a "fair" contract if he finds out that it's better to be a big fish in a small pond than go to somewhere like Colorado or Edmonton where he's no longer a fan favorite star or a household name that will get 18-20 minutes a night.